Herbicidal substituted benzoylpyrazoles

ABSTRACT

The invention relates to benzoylpyrazoles of the general formula (I),  
                 
 
     in which Q, R 1 , R 2 , R 3 , R 4 , R 5 , Y and Z are as defined in the disclosure, to processes and intermediates for their preparation, and to their use as herbicides.

[0001] The invention relates to novel substituted benzoylpyrazoles, to aprocess for their preparation and to their use as herbicides.

[0002] It is already known that certain substituted benzoylpyrazoles,such as the compounds N-[2,6-dichloro-3-[(5-hydroxy- 1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-acetamide,[2,6-dichloro-3-[(5-hydroxy- 1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-carbamic acid methyl ester,N′-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-N,N-diethyl-urea,[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-carbamicacid methyl ester, N′-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N-diethyl-urea,N-[3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-acetamide,N-[3-[(5-hydroxy- 1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-propanamide,N-[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-acetamide,N′-[2-chloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-6-methyl-sulphonyl-phenyl]-N,N-diethyl-urea,N-[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-formamide,[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-carbamicacid methyl ester,N-[2-chloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-acetamide,N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-acetamide,N-[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-2,2,2-trifluoro-acetamide,N-[3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-2,2,2-trifluoro-acetamide,N-[3-[(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-N-methyl-formamide,N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N-methyl-carbamicacid methyl ester,N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N′-diethyl-N-methyl-urea andN-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-N-methyl-carbamicacid methyl ester (cf. JP-A-11292849—cited in Chem. Abstracts131:286507) have herbicidal properties (cf. also EP-A-352543, U.S. Pat.No. 5,846,907, WO-A-96/26206, WO-A-97/41105, WO-A-97/41116,WO-A-97/41117, WO-A-97/41118, WO-A-97/46530, WO-A-98/28981,WO-A-98/31681, WO-A-98/31682, WO-A-99/07697, WO-A-99/10328,WO-A-00/58306). However, the activity of these compounds is not entirelysatisfactory.

[0003] This invention, accordingly, provides the novel substitutedbenzoylpyrazoles of the general formula (I)

[0004] in which

[0005] Q represents O (oxygen) or S (sulphur),

[0006] R¹ represents in each case optionally substituted alkyl, alkenyl,alkinyl or cycloalkyl,

[0007] R² represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,or represents in each case optionally substituted alkyl, alkoxy,alkylthio, alkoxycarbonyl or cycloalkyl,

[0008] R³, R⁴ independently of one another represent hydrogen, nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or in each caseoptionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, dialkylamino, dialkylaminocarbonyl ordialkylaminosulphonyl,

[0009] R⁵ represents hydrogen or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylthio,arylsulphinyl, arylsulphonyl, arylalkyl, or represents the grouping—C(Q)—Z,

[0010] Y represents hydrogen or in each case optionally substitutedalkyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkenyl, alkenylsulphonyl,alkenylcarbonyl, alkinyl, alkinylcarbonyl, cycloalkyl,cycloalkylcarbonyl, cycloalkylalkyl, phenyl, phenylsulphonyl,phenylcarbonyl, phenylalkyl, phenylalkylsulphonyl, phenylalkylcarbonylor phenylcarbonylalkyl, and

[0011] Z represents amino, cyanoamino, nitroamino, hydroxyamino,hydrazino,

[0012] represents in each case cyano-, alkoxy-, alkylthio-,alkylsulphinyl- or alkylsulphonyl-substituted alkyl, alkoxy, alkylthioor alkylamino,

[0013] represents in each case optionally substituted alkylcarbonyl,alkoxycarbonyl, alkoxyamino, alkylhydrazino, alkylcarbonylhydrazino,alkoxycarbonylhydrazino, alkylsulphonylhydrazino, N-alkyl-alkoxyamino,dialkylhydrazino, alkenyloxy, alkenylamino, alkenyloxyamino, aLkinyloxy,alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino,cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy,arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino, the grouping —N=(heterocyclyl),heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio orheterocyclylalkylamino,

[0014] including all possible tautomeric forms of the compounds of thegeneral formula (I) and the possible salts of the compounds of thegeneral formula (I).

[0015] Preferred meanings of the radicals or groupings present in theformulae given above and below are defined below.

[0016] Q preferably represents O.

[0017] R¹ preferably represents optionally cyano-, halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl- substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally cyano- or halogen-substituted alkenylor alkinyl having in each case 2 to 6 carbon atoms, or representsoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having3 to 6 carbon atoms.

[0018] R² preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy or alkoxycarbonylhaving in each case up to 6 carbon atoms, represents optionallyhalogen-substituted alkylthio having 1 to 6 carbon atoms, or representsoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having3 to 6 carbon atoms.

[0019] R³, R⁴ independently of one another preferably representhydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen,represent in each case optionally halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbonatoms in the alkyl groups, or represent alkylamino, dialkylamino,dialkylaminocarbonyl or dialkylaminosulphonyl having in each case up to4 carbon atoms in the alkyl groups.

[0020] R⁵ preferably represents hydrogen, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl having in each case 1 to 6carbon atoms in the alkyl groups, represents in each case optionallycyano- or halogen-substituted alkenyl or alkinyl having in each case 3to 6 carbon atoms in the alkenyl and alkinyl groups, respectively,represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in eachcase 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1to 4 carbon atoms in the alkyl moiety, represents in each caseoptionally nitro- cyano-, C₁-C₄-alkyl-, C₁-C₄-halogenalkyl-,C₁-C₄-alkoxy-, C₁-C₄-halogenalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenalkylthio-, C₁-C₄-alkylsulphinyl-,C₁-C₄-halogenalkylsulphinyl-, C₁-C₄-alkylsulphonyl- orC₁-C₄-halogenalkyl-sulphonyl-substituted aryl, arylthio, arylsulphinyl,arylsulphonyl or arylalkyl having in each case 6 or 10 carbon atoms inthe aryl groups and, if appropriate, 1 to 4 carbon atoms in the alkylmoiety, or represents the grouping —Q(Q)—Z.

[0021] Y preferably represents hydrogen, represents optionally cyano-,carbamoyl-, halogen-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedalkyl having 1 to 6 carbon atoms, represents optionallyhalogen-substituted alkylsulphonyl having 1 to 6 carbon atoms,represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl oralkylaminocarbonyl having in each case 1 to 6 carbon atoms in the alkylgroups, represents dialkylaminocarbonyl having 1 to 4 carbon atoms inthe alkyl groups, represents in each case optionally cyano- orhalogen-substituted alkenyl, alkenylcarbonyl, alkinyl or alkinylcarbonylhaving in each case up to 6 carbon atoms, represents optionallyhalogen-substituted alkenylsulphonyl having up to 6 carbon atoms,represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkylcarbonyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl groups and, if appropriate, 1 to 3 carbon atoms in the alkylmoiety, or represents in each case optionally nitro-, cyano-,carbamoyl-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-or C₁-C₄-halogenalkoxy-substituted phenyl, phenylsulphonyl,phenylcarbonyl, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl-sulphonyl,phenyl-C₁-C₄-alkyl-carbonyl or phenylcarbonyl-C₁-C₄-alkyl.

[0022] Z preferably represents amino, cyanoamino, nitroamino,hydroxyamino, hydrazino,

[0023] represents in each case cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy,alkylthio or alkylamino having in each case 1 to 6 carbon atoms,represents C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl,

[0024] represents in each case optionally cyano-, halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkoxyamino, alkylhydrazino,alkylcarbonylhydrazino, alkoxycarbonylhydrazino oralkylsulphonylhydrazino having in each case 1 to 6 carbon atoms in thealkyl groups, represents N-alkyl-alkoxyamino or dialkylhydrazino havingin each case 1 to 4 carbon atoms in the alkyl groups,

[0025] represents in each case optionally halogen-substitutedalkenyloxy, alkenylamino, alkenyloxyamino, alkinyloxy or alkinylaminohaving in each case 2 to 6 carbon atoms,

[0026] represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylamino,cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy orcycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkylmoiety,

[0027] represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenalkoxy- or C₁-C₄-alkoxy-carbonyl-substituted aryl,arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino,arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylaminohaving in each case 6 or 10 carbon atoms in the aryl group and, ifappropriate, 1 to 4 carbon atoms in the alkyl moiety,

[0028] or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted monocyclic or bicyclic heterocyclyl,heterocyclyloxy, heterocyclylthio, heterocyclylamino, the grouping—N=(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy,heterocyclylalkylthio or heterocyclylalkylamino where in each case theheterocyclyl grouping contains up to 10 carbon atoms and additionally atleast one heteroatom selected from the group consisting of nitrogen (butat most 5 N atoms), oxygen (but at most 2 O atoms), sulphur (but at most2 S atoms), SO or SO₂ and, if appropriate, additionally one groupselected from the group consisting of oxo (C═O), thioxo (C═S), imino(C═NH), cyanoimino (C═N—CN), nitroimino (C═N—NO₂) and where, ifappropriate, the alkyl moiety contains 1 to 4 carbon atoms.

[0029] R¹ particularly preferably represents in each case optionallycyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or,t-butyl, represents in each case optionally cyano-, fluorine-, chlorine-or bromine-substituted propenyl, butenyl, propinyl or butinyl, orrepresents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0030] R² particularly preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine, bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents ineach case optionally fluorine- and/or chlorine-substituted methylthio,ethylthio, n- or i-propylthio, or represents in each case optionallycyano-, fluorine-, chlorine-, bromine- methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0031] R³, R⁴ independently of one another particularly preferablyrepresent hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,fluorine, chlorine, bromine, iodine, represent in each case optionallyfluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, representmethylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl,diethylaminocarbonyl, dimethylaminosulphonyl or diethylaminosulphonyl.

[0032] R⁵ particularly preferably represents hydrogen, represents ineach case optionally-cyano-, fluorine-, chlorine-, bromine-, methoxy-,ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, n-, i-, s-, or t-pentyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, represents dimethylamino or diethylamino, represents ineach case optionally fluorine-, chlorine- and/or bromine-substitutedethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl, butinyl orpentinyl, represents in each case optionally cyano-, fluorine-,chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl, phenylthio, phenylsulphinyl,phenylsulphonyl, naphthyl, phenylnethyl, phenylethyl, naphthylmethyl ornaphthylethyl or represents the grouping—C(Q)—Z.

[0033] Y particularly preferably represents hydrogen, represents in eachcase optionally cyano-, carbamoyl-, fluorine-, chlorine-, methoxy-,ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, representsin each case optionally fluorine- and/or chlorine-substitutedmethylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl,represents dimethylaminocarbonyl or diethylaminocarbonyl, represents ineach case optionally cyano-, fluorine-, chlorine- or bromine-substitutedpropenyl, butenyl, propenylcarbonyl, butenylcarbonyl, propinyl, butinyl,propinylcarbonyl or butinylcarbonyl, represents in each case optionallyfluorine- and/or chlorine-substituted propenylsulphonyl orbutenylsulphonyl, represents in each case optionally cyano-, fluorine-,chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, carbamoyl-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl,phenylsulphonyl, phenylcarbonyl, phenylmethyl, phenylethyl,phenylmethylsulphonyl, phenylmethylcarbonyl or phenylcarbonylmethyl.

[0034] Z particularly preferably represents amino, cyanoamino,nitroamino, hydroxyamino, hydrazino,

[0035] represents in each case cyano-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino,n- or i-propylamino, n-, i-, s- or t-butylamino,

[0036] represents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- ori-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substitutedmethoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- ort-butoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino,n-, i-, s- or t-butylhydrazino, represents N-methylmethoxyamino ordimethylhydrazino,

[0037] represents in each case optionally fluorine-, chlorine- and/orbromine-substituted propenyloxy, butenyloxy, pentenyloxy, propenylthio,butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino,propenyloxyamino, butenyloxyamino, pentenyloxyamino, propinyloxy,butinyloxy, pentinyloxy, propinylamino, butinylamino or pentinylamino,

[0038] represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino,cyclohexylamino, cyclopropylhydrazino, cyclobutylhydrazino,cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino,

[0039] represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-,n- or i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl,naphthyloxy, naphthylthio, naphthylamino, phenylmethyl, phenylethyl,phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio,phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl,naphthylmethoxy, naphthylethoxy, naphthylmethylamino ornaphthylethylamino, or

[0040] represents in each case optionally nitro-, cyano-, fluorine-,chlorine- bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-, cyclohexyl-,difluoromethyl-, trifluormethyl-, dichloromethyl-, trichloromethyl,chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-,s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedmonocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,the grouping —N=(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy orheterocyclylalkylamino from the group consisting of furyl, furyloxy,furylamino, furylmethyl, furylmethoxy, furylmethylamino,tetrahydrofuryl, tetrahydrofuryloxy, tetrahydrofurylamino,tetrathydrofurylmethyl, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanylmethyl,dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolinyl, imidazolylmethyl, iimidazolinylmethyl, oxoimidazolinyl,2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl (oxazolinyl),tetrahydrooxazolyl (oxazolidinyl), isoxazolyl, dihydroisoxazolyl(isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),tetrahydro-(2H)-1,2-oxazin-2-yl, oxazolylmethyl, thiazolyl,dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl),thiazolimino, thiazolylmethyl, dihydrothiazolyl (thiazolinyl),tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl,cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino,oxotriazolinyl, oxotetrazolinyl, dioxanyl, dioxanylmethyl,dioxanylmethoxy, dioxanylmethylamino, dithianyl, dithianylmethyl,dithianylmethoxy, dithianylmethylamino, triazolylamino, piperidinyl,piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl,2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl,oxomorpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy,pyridinylamino, 2-(1H)-pyridinimino, pyridinylmethyl, pyridinylmethoxy,pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy.

[0041] R¹ very particularly preferably represents methyl, ethyl, n- ori-propyl, cyclopropyl, cyclopentyl or cyclohexyl.

[0042] R² very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl,represents in each case optionally fluorine- and/or chlorine-substitutedmethylthio or ethylthio, or represents optionally fluorine-, chlorine-or methyl-substituted cyclopropyl.

[0043] R³, R⁴ independently of one another very particularly preferablyrepresent hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl,ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl,trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.

[0044] R⁵ very particularly preferably represents hydrogen, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n- or i-butyl,represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino,ethylamino, n- or i-propylamino or dimethylamino, represents in eachcase optionally fluorine- and/or chlorine-substituted propenyl, butenyl,propinyl or butinyl, represents in each case optionally cyano-,fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-, trifluoromethyl-,methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylthio, phenylsulphinyl,phenylsulphonyl, phenylmethyl or phenylethyl, or represents the grouping—C(Q)—Z.

[0045] Y very particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, methoxy-, ethoxy-,methoxycarbonyl- or ethoxycarbonyl-substituted methyl or ethyl,represents in each case optionally fluorine- and/or chlorine-substitutedmethylsulphonyl or ethylsulphonyl, represents in each case optionallycyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted acetyl,propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl orethylaminocarbonyl, represents dimethylaminocarbonyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted propenyl,propenylcarbonyl, propinyl or propinylcarbonyl, represents in each caseoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylsulphonyl, phenylcarbonyl,phenylmethyl, phenylmethylsulphonyl, phenylmethylcarbonyl orphenylcarbonylmethyl.

[0046] Z very particularly preferably represents amino, cyanoamino,hydrazino,

[0047] represents in each case optionally cyano-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n-or i-propylamino,

[0048] represents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- ori-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substitutedmethoxyamino, ethoxyamino, n- or i-propoxyamino, methylhydrazino-,ethylhydrazino-, n- or i-propylhydrazino, n-, i-, s- ort-butylhydrazino, N-methyl-methoxyamino or dimethylhydrazino,

[0049] represents in each case optionally fluorine- and/orchlorine-substituted propenyloxy, butenyloxy, propenylthio, butenylthio,propenylamino, butenylamino, propenyloxyamino, butenyloxyamino,propinyloxy, butinyloxy, propinylamino or butinylamino,

[0050] represents in each case optionally cyano-, fluorine-, chlorine-or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino,

[0051] represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-; ethoxycarbonyl-,n- or i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl,phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio,phenylethylthio, phenylmethylamino or phenylethylamino,

[0052] or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- ort-butyl-, cyclohexyl-, difluoromethyl-, trifluoromethyl-,dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-,fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- ori-propylthio-, difluoromethylthio-, trifluoromethylthio-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedmonocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,the grouping —N=(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy orheterocyclylalkylamino from the group consisting of furyl, furyloxy,furylamino, furylmethyl, furylmethoxy, furylmethylamino,tetrahydrofuryl, tetrahydrofuryloxy, tetrahydrofurylamino,tetrahydrofurylmethyl, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanylmethyl,dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolinyl, imidazolylmethyl, imidazolinylmethyl,2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl(oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl,dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),tetra-hydro-(2H)-1,2-oxazin-2-yl, thiazolyl, thiazolylmethyl,dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl),thiazolimino, oxothiazolidinyl, cyanoiminothiazolidinyl,oxadiazolylamino, thiadiazolylamino, oxotriazolinyl, oxotetrazolinyl,dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino,dithianyl, dithianylmethyl, dithianylmethoxy, dithianylmethylamino,triazolylamino, piperidinyl, piperidinylamino, oxopiperidinyl,2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxo-morpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,2-(1H)-pyridinimino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl,pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy.

[0053] A very particularly preferred group are those compounds of thegeneral formula (I) in which

[0054] Q represents O or S,

[0055] R¹ represents methyl, ethyl, n- or i-propyl,

[0056] R² represents hydrogen, methyl, ethyl, methoxycarbonyl,ethoxycarbonyl, methylthio or ethylthio,

[0057] R³, R⁴ independently of one another represent hydrogen, nitro,cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl,

[0058] R⁵ represents hydrogen, represents methyl, ethyl, n- or i-propyl,represents methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl orethylsulphonyl, represents in each case optionally fluorine- and/orchlorine-substituted propenyl, butenyl, propinyl or butinyl, orrepresents cyclopropyl,

[0059] Y represents hydrogen, represents in each case optionally cyano-,fluorine-, methoxy-, ethoxy-, methoxycarbonyl- orethoxycarbonyl-substituted methyl or ethyl, represents in each caseoptionally fluorine- and/or chlorine-substituted methylsulphonyl orethylsulphonyl, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted acetyl, propionyl,methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl orethylaminocarbonyl, represents dimethylaminocarbonyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted propenyl,propenylcarbonyl, propinyl or propinylcarbonyl, represents in each caseoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylsulphonyl, phenylcarbonyl,phenylmethyl, phenylmethylsulphonyl, phenylmethylcarbonyl orphenylcarbonylmethyl and

[0060] Z represents amino, cyanoamino, hydrazino, representsmethoxyamino, ethoxyamino, n- or i-propoxyamino, methylhydrazino,ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino,represents N-methylmethoxyamino or dimethylhydrazino,

[0061] represents in each case optionally fluorine- and/orchlorine-substituted propenyloxy, butenyloxy, propenylthio, butenylthio,propenylamino, butenylamino, propenyloxyamino, butenyloxyamino,propinyloxy, butinyloxy, propinylamino or butinylamino,

[0062] represents in each case optionally cyano-, fluorine-, chlorine-or methyl-substituted cyclopropyl, cyclopentyl, cyclohexyl,cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino,cyclopentylamino, cyclohexylamino, cyclohexylhydrazino,cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl,cyclopropylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino,

[0063] represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-,n- or i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl,phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio,phenylethylthio, phenylmethylamino or phenylethylamino, or

[0064] represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-, cyclohexyl-,difluoromethyl-, trifluoromethyl-, dichloromethyl-, trichloromethyl-,chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, difluoromethylthio-,trifluoromethylthio-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl,heterocyclyloxy, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy or heterocyclylalkylamino from the group consistingof furyl, fuloxy, furylamino, furylmethyl, furylmethoxy,furylmethylamino, tetrahydrofuryl, tetrahydrofuryloxy,tetrahydrofurylamino, tetrahydrofurylmethyl, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanylmethyl,dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxo-pyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolinyl, imidazolylmethyl, imidazolinylmethyl,2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl(oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl,dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),thiazolyl, thiazolylmethyl, dihydrothiazolyl (thiazolinyl),tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl,cyanoiminothiazolidinyl, oxotriazolinyl, oxotetrazolinyl, dioxanyl,dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, dithianyl,dithianylmethyl, dithianylmethoxy, dithianylmethylamino, triazolylamino,piperidinyl, piperidinylamino, oxopiperidinyl,2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxomorpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy,pyrimidinylmethyl, pyrimidinylmethoxy.

[0065] Particular emphasis is given to the compounds of the formulae(I-1) to (I-3):

[0066] Here, Q, R¹, R², R³, R⁴, R⁵, Y and Z in each case have themeanings given above as being preferred, particularly preferred or veryparticularly preferred.

[0067] Particular emphasis is also given to the compounds of theformulae (I-a), (I-b) and (I-c):

[0068] Here, Q, Z, R¹, R², R³, R⁴ and R⁵ in each case have the meaningsgiven above as being preferred, particularly preferred or veryparticularly preferred.

[0069] The general or preferred radical definitions given above applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

[0070] The radical definitions can be combined with one another asdesired, i.e. including combinations between the given preferred ranges.

[0071] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred.

[0072] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0073] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0074] Unless defined otherwise, the following definitions apply in thedefinitions given above and below:

[0075] Saturated or unsaturated hydrocarbon chains, such as alkyl,alkanediyl, alkenyl or alkinyl, are in each case straight-chain orbranched, including in combination with heteroatoms, such as, forexample, in alkoxy, alkylthio or alkylamino. Unless indicated otherwise,preference is given to hydrocarbon chains having 1 to 6 carbon atoms.

[0076] Aryl represents aromatic mono- or polycyclic hydrocarbon rings,such as, for example, phenyl, naphthyl, anthranyl, phenanthryl,preferably phenyl or naphthyl, in particular phenyl.

[0077] Heterocyclyl represents saturated, unsaturated or aromatic cycliccompounds in which at least one ring atom is a heteroatom, i.e. an atomdifferent from carbon. If the ring contains a plurality of heteroatoms,these can be identical or different. Preferred heteroatoms are oxygen,nitrogen and sulphur. If the ring contains a plurality of oxygen atoms,these are not adjacent. If appropriate, the cyclic compounds may form apolycyclic ring system together with further carbocyclic or heterocyclicfused-on or bridged rings. A polycyclic ring system can be attached viathe heterocyclic ring or a fused-on carbocyclic ring. Preference isgiven to mono- or bicyclic ring systems, in particular to monocyclicring systems having 5 or 6 ring members and to bicyclic ring systemshaving 7 to 9 ring members.

[0078] Cycloalkyl represents saturated, carbocyclic compounds which, ifappropriate, form a polycyclic ring system together with furthercarbocyclic fused-on or bridged rings.

[0079] Unless indicated otherwise, preference is given to cyclopropyl,cyclopentyl and cyclohexyl.

[0080] The novel substituted benzoylpyrazoles of the general formula (I)have strong and selective herbicidal activity.

[0081] The novel substituted benzoylpyrazoles of the general formula (I)obtained when

[0082] a) pyrazoles of the general formula (II)

[0083]  in which

[0084]  R¹, R² and Y are as defined above

[0085]  are reacted with substituted benzoic acids of the generalformula (III)

[0086]  in which

[0087]  Q, R³, R⁴, R⁵ and Z are as defined above

[0088]  or with reactive derivatives thereof, such as, for example, thecorresponding acid halides, acid anhydrides, acid cyanides or esters,

[0089] if appropriate in the presence of a dehydrating agent, ifappropriate in the presence of one or more reaction auxiliaries and ifappropriate in the presence of one or more diluents,

[0090] or when

[0091] (b) substituted benzoylpyrazoles of the general formula (Ia)

[0092]  in which

[0093]  Q. R¹, R², R³, R⁴, R⁵ and Z are as defined above,

[0094]  are reacted with compounds of the general formula (IV)

X—Y  (IV)

[0095]  in which

[0096]  Y is as defined above, except for hydrogen, and

[0097]  X represents halogen,

[0098]  or, if appropriate, with corresponding acid anhydrides,isocyanates or isothiocyanates

[0099] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,

[0100] and, if appropriate, the resulting compounds of the formula (I)are subsequently subjected, in a customary manner, to electrophilic ornucleophilic substitution reactions and/or oxidation or reductionreactions, or the compounds of the formula (I) are, in a customarymanner, converted into salts.

[0101] In principle, the novel substituted benzoylpyrazoles of thegeneral formula (I) can also be obtained as shown schematically below:

[0102] (c) by reacting aminobenzoylpyrazoles of the general formula (V)with halogeno-(thio)carbonyl compounds of the general formula (VI) or,if appropriate, with corresponding iso(thio)cyanates (here, Q, R¹, R²,R³, R⁴, R⁵, Y and Z are as defined above, X represents halogen):

[0103] (d) by reacting iso(thio)cyanatobenzoylpyrazoles of the generalformula (VII) with nucleophilic compounds of the general formula (VII)(here, Q, R¹, R², R³, R⁴, Y and Z are as defined above):

[0104]

[0105] Using, for example, 3-chloro-5-hydroxy-1-methyl-pyrazol and3-[(cyclopropylaminocarbonyl)-(methylamino)]-5-fluoro-benzoic acid asstarting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the formula schemebelow:

[0106] Using, for example, 2-methoxy-ethylN-[3-chloro-4-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenyl]-N-ethyl-carbamateand benzoyl chloride as starting materials, the course of the reactionin the process (b) according to the invention can be illustrated by theformula scheme below:

[0107] The formula (II) provides a general definition of the pyrazolesto be used as starting materials in the process (a) according to theinvention for preparing compounds of the general formula (I). In thegeneral formula (II), R¹, R² and Y preferably have those meanings whichhave already been mentioned above, in connection with the description ofthe compounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred or very particularly preferredfor R¹, R² and Y.

[0108] The starting materials of the general formula (II) are knownand/or can be prepared by processes known per se (cf. EP-A-240 001).

[0109] The formula (III) provides a general definition of thesubstituted benzoic acids further to be used as starting materials inthe process (a) according to the invention. In the formula (III) Q, R³,R⁴, R⁵ and Z preferably have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe formula (I) according to the invention, as being preferred,particularly preferred or very particularly preferred for Q, R³, R⁴, R⁵and Z.

[0110] The starting materials of the general formula (III) are knownand/or can be prepared by processes per se (cf. JP-A-112 92 849 andPreparation Examples).

[0111] The substituted benzoic acids of the general formula (III) areobtained when benzoic acid esters of the general formula (IIIa)

[0112] in which

[0113] Q, R³, R⁴, R⁵ and Z are as defined above and

[0114] R represents alkyl, in particular methyl or ethyl,

[0115] are reacted with water, if appropriate in the presence of ahydrolysis auxiliary, such as, for example, aqueous sodium hydroxidesolution, and if appropriate in the presence of a diluent, such as, forexample, tetrahydrofuran, at temperatures between 0° C. and 100° C. (cf.the Preparation Examples).

[0116] The benzoic acid esters of the general formula (IIIa) required asprecursors are known and/or can be prepared by processes known per se(cf. JP-A-112 92 849 and Preparation Examples).

[0117] The benzoic acid esters of the general formula (IIIa) areobtained when

[0118] (α) aminobenzoic acid esters of the general formula (IX)

[0119]  in which

[0120]  Q, R³, R⁴, R⁵ and Z are as defined above and

[0121]  R represents alkyl, in particular methyl or ethyl,

[0122]  are reacted with halogeno(thio)carbonyl compounds of the generalformula (VI)

[0123]  in which

[0124]  Q and Z are as defined above and

[0125]  X represents halogen, in particular fluorine, chlorine orbromine,

[0126] or, if appropriate, with the corresponding iso(thio)cyanates

[0127] if appropriate in the presence of an acid acceptor, such as, forexample, potassium carbonate or triethylamine, and if appropriate in thepresence of a diluent, such as, for example, methyl isobutyl ketone oracetonitrile, at temperatures between 0° C. and 100° C. (cf. thePreparation Examples),

[0128] or when

[0129] (β) iso(thio)cyanatobenzoic acid esters of the general formula(X)

[0130]  in which

[0131]  Q, R³ and R⁴ are as defined above and

[0132]  R represents alkyl, in particular methyl or ethyl,

[0133]  are reacted with nucleophilic compounds of the general formula(VIII)

[0134]  in which

[0135]  Z is as defined above,

[0136]  if appropriate in the presence of a reaction auxiliary, such as,for example, triethylamine, and if appropriate in the presence of adiluent, such as, for example, acetonitrile or toluene, at temperaturesbetween 10° C. and 120° C. (cf. the Preparation Examples).

[0137] The formula (Ia) provides a general definition of the substitutedbenzoylpyrazoles to be used as starting materials in the process (b)according to the invention for preparing compounds of the generalformula (I). In the general formula (Ia), Q, R¹, R², R³, R⁴, R⁵ and Zpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for Q, R¹, R², R³, R⁴, R⁵ andZ.

[0138] The starting materials of the general formula (Ia) are novelcompounds according to the invention; they can be prepared by process(a) according to the invention.

[0139] The formula (IV) provides a general definition of the compoundsfurther to be used as starting materials in the process (b) according tothe invention. In the general formula (IV), Y preferably has thatmeaning which has already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred or veryparticularly preferred for Y; X preferably represents fluorine,chlorine, bromine or iodine, in particular chlorine or bromine.

[0140] The starting materials of the general formula (IV) are knownchemicals for synthesis.

[0141] The formulae (V) and (VI) provide general definitions of thecompounds further to be used as starting materials in the process (c)according to the invention for preparing compounds of the generalformula (I). In the general formulae (V) and (VI), Q, R¹, R², R³, R⁴,R⁵, X and Z preferably have that meaning which has already beenmentioned above, in connection with the description of the generalformula (I), as being preferred, particularly preferred or veryparticularly preferred for Q, R¹, R², R³, R⁴, R⁵, X and Z. The startingmaterials of the general formula (VI) are known organic compounds. Thestarting materials of the general formula (V) can be prepared byprocesses known per se.

[0142] The formulae (VII) and (VIII) provide general definitions of thecompounds to be used as starting materials in the process (d) accordingto the invention for preparing compounds of the general formula (I). Inthe general formulae (VII) and (VIII), Q, R¹, R², R³, R⁴, R⁵, Y and Zpreferably have that meaning which has already been mentioned above, inconnection with the description of the general formula (I), as beingpreferred, particularly preferred or very particularly preferred.

[0143] The starting materials of the general formula (VIII) are knownchemicals for synthesis. The starting materials of the general formula(VII) can be prepared by processes known per se.

[0144] The formula (IX) provides a general definition of the compoundsto be used as starting materials in the process (α) according to theinvention for preparing compounds of the general formula (IIIa). In thegeneral formula (IX), R³, R⁴ or R⁵ preferably have that meaning whichhas already been mentioned above, in connection with the description ofthe general formula (I), as being preferred, particularly preferred orvery particularly preferred.

[0145] The formula (X) provides a general definition of the compounds tobe used as starting materials in the process (β) according to theinvention for preparing compounds of the formula (IIIa). In the generalformula (X), Q, R³ and R⁴ preferably have that meaning which has alreadybeen mentioned above, in connection with the description of the generalformula (I), as being preferred, particularly preferred or veryparticularly preferred.

[0146] The starting materials of the general formula (X) can be preparedby processes know per se.

[0147] The process (a) according to the invention for preparing novelsubstituted benzoylpyrazoles of the general formula (I) is preferablycarried out using a dehydrating agent. Suitable dehydrating agents arethe customary chemicals suitable for binding water.

[0148] Examples which may be mentioned are dicyclohexylcarbodiimide,propanephosphonic anhydride and carbonyl-bis-imidazole.

[0149] Dehydrating agents which may be mentioned as being particularlysuitable are dicyclohexylcarbodiimide and propanephosphonic anhydride.

[0150] The process (a) according to the invention for preparing thenovel substituted benzoylpyrazoles of the general formula (I) is, ifappropriate, carried out using a reaction auxiliary.

[0151] Examples of suitable reaction auxiliaries which may be mentionedare sodium cyanide, potassium cyanide, acetone cyanohydrin,2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilyl cyanide.

[0152] A reaction auxiliary which may be mentioned as being particularlysuitable is trimethylsilyl cyanide.

[0153] The processes (a) and (b) according to the invention arepreferably carried out using one or more reaction auxiliaries. Suitablereaction auxiliaries for the processes (a) and (b) according to theinvention are, in general, the customary inorganic or organic bases oracid acceptors. These preferably include alkali metal or alkaline earthmetal acetates, amides, carbonates, bicarbonates, hydrides, hydroxidesor alkoxides, such as, for example, sodium acetate, potassium acetate orcalcium acetate, lithium amide, sodium amide, potassium amide or calciumamide, sodium carbonate, potassium carbonate or calcium carbonate,sodium bicarbonate, potassium bicarbonate or calcium bicarbonate,lithium hydride, sodium hydride, potassium hydride or calcium hydride,lithium hydroxide, sodium hydroxide, potassium hydroxide or calciumhydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- ort-butoxide; furthermore also basic organic nitrogen compounds, such as,for example, trimethylamine, triethylamine, tripropylamine,tributylamine, ethyl-diisopropylamine, N,N-dimethylcyclohexylamine,dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline,N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine,N-methyl-piperidine, N-ethylpiperidine, N-methyl-morpholine,N-ethyl-morpholine, 1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene(DBU).

[0154] Further reaction auxiliaries suitable for the processes (a) and(b) according to the invention are phase-transfer catalysts. Examples ofsuch catalysts which may be mentioned are:

[0155] Tetrabutylammonium bromide, tetrabutylammonium chloride,tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate,methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride,hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride,benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide,benzyl-triethylammonium hydroxide, benzyltributylammonium chloride,benzyl-tributylammonium bromide, tetrabutylphosphonium bromide,tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide,butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide,tetraphenylphosphonium bromide.

[0156] The processes according to the invention for preparing thecompounds of the general formula (I) are in each case preferably carriedout using one or more diluents. Suitable diluents for carrying out theprocesses (a) and (b) according to the invention are, in addition towater, especially inert organic solvents. These include, in particular,aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons,such as, for example, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,chloroform, carbon tetrachloride; ethers, such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethylether or ethylene glycol diethyl ether; ketones, such as acetone,butanone or methyl isobutyl ketone; nitriles, such as acetonitrilepropionitrile or butyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethyl-phosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethyelene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

[0157] When carrying out the processes (a) and (b) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperaturesbetween 0° C. and 150° C., preferably between 10° C. and 120° C.

[0158] The processes according to the invention are generally carriedout under atmospheric pressure. However, it is also possible to carryout the processes according to the invention under elevated or reducedpressure - in general between 0.1 bar and 10 bar.

[0159] For carrying out the processes according to the invention, thestarting materials are generally employed in approximately equimolaramounts. However, it is also possible to use a relatively large excessof one of the components. The reaction is generally carried out in asuitable diluent in the presence of a reaction auxiliary, and thereaction mixture is generally stirred at the required temperature for anumber of hours. Work-up is carried out by customary methods (cf. thePreparation Examples).

[0160] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

[0161] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0162] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lam ium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbaria, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0163] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0164] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0165] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

[0166] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0167] The active compounds according to the invention are suitable,depending on the concentration, for the total control of weeds, forexample on industrial terrain and rail tracks, and on paths and areaswith and without tree plantings. Similarly, the active compoundsaccording to the invention can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

[0168] The compounds of the formula (I) according to the invention havestrong herbicidal. activity and a broad active spectrum when used on thesoil and on above-ground parts of plants. To a certain extent they arealso suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and di-cotyledonous crops, bothby the pre-emergence and by the post-emergence method.

[0169] At certain concentrations or application rates, the activecompounds according to the invention can also be employed forcontrolling animal pests and fungal or bacterial plant diseases. Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

[0170] According to the invention, it is possible to treat all plantsand parts of plants. Plants are to be understood here as meaning allplants and plant populations such as desired and undesired wild plantsor crop plants (including naturally occurring crop plants). Crop plantscan be plants which can be obtained by conventional breeding andoptimization methods or by biotechnological and genetic engineeringmethods or combinations of these methods, including the transgenicplants and including plant cultivars which can or cannot be protected byplant breeders certificates. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of plants,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stems, tniks, flowers, fruit-bodies, fruits andseeds and also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

[0171] The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

[0172] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic substancesimpregnated with active compound, and microencapsulations in polymericsubstances.

[0173] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is to say liquidsolvents and/or solid carriers, optionally with the use of surfactants,that is to say emulsifiers and/or dispersants and/or foam-formers.

[0174] If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Liquid solvents whichare mainly suitable are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and water.

[0175] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

[0176] Tackifiers, such as carboxylmethylcellulose, natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0177] It is possible to use colorants, such as inorganic pigments, forexample iron oxide, titanium oxide, Prussian blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients, such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0178] The formulations generally comprise between 0.1 and 95 per centby weight of active compound, preferably between 0.5 and 90%.

[0179] For controlling weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides and/or substances which improve thecompatibility with crop plants (“safeners”), finished formulations ortank mixes being possible. Also possible are mixtures with weed-killerscomprising one or more known herbicides and a safener.

[0180] Possible components for the mixtures are known herbicides, forexample acetochlor, acifluorfen (-sodium), aclonifen, alachlor,alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulphuron,anilofos, asulam, atrazine, azafenidin, azimsulphuron, beflubutarnid,benazolin (-ethyl), benfuresate, bensulphuron (-methyl), bentazon,benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl),bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim,bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chloritrofen, chlorsulphuron, chlortoluron, cinidon (-ethyl), cinmethylin,cinosulphuron, clefoxydim, clethodim, clodinafop (-propargyl),clomazone, clomeprop, clopyralid, clopyrasulphuron (-methyl),cloransulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate,cyclosulphamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB,desmedipham, diallate, dicamba, dichlorprop (-P), diclofop (-methyl),diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulphuron (-methyl), ethofumesate, ethoxyfen, ethoxysulphuron,etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulphuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,flumetsulaam, flumiclorac (-pentyl), flumioxazin, flumipropyn,flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),flupoxam, flupropacil, flurpyrsulphuron (-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen,foramsulphuron, glufosinate (-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop (-ethoxy-ethyl, -P-methyl),hexazinone, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic,imazapyr, imazaquin, imazethapyr, imazosulphuron, iodosulphuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron,isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil,linuron, MCPA, mecoprop, mefenacet, mesosulphuron, mesotrione,metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron,(alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulphuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon,nicosulphuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon,oxasulphuron, oxaziclomefone, oxyfluorfen, paraquat, pelargon acid,pendimetha in, pendralin, pentoxazone, phenmedipham, picolinafen,piperophos, pretilachlor, primisulphuron (-methyl), profluazol,prometryn, propachlor, propanil, propaquizafop, propisochlor,procarbazone (-sodium), propyzamide, prosulphocarb, prosulphuron,pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulphuron (-ethyl),pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl),rimsulphuron, sethoxydim, simazine, simetryn, sulcotrione,sulphentrazone, sulphometuron (-methyl), sulphosate, sulphosulphuron,tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn,thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulphuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate,triasulphuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulphuron, triflusulphuron (-methyl), tritosulphuron.

[0181] Furthermore suitable for the mixtures are known softeners, forexample AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl),cyometrinil, 2,4-D, DKA-24, dichlormid, dymron, fenclorim, fenchlorazol(-ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA,mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292,R-29148.

[0182] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0183] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

[0184] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before sowing.

[0185] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0186] As already mentioned above, it is possible to treat all plantsand their parts according to the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding, such as crossing or protoplast fusion,and parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

[0187] Particularly preferably, plants of the plant cultivars which arein each case commercially available or in use are treated according tothe invention. Plant cultivars are to be understood as meaning plantshaving certain properties (“traits”) and which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.They can be cultivars, bio- or genotypes.

[0188] Depending on the plant species or plant cultivars, their locationand growth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention—also in combination with other agro-chemical activecompounds—, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

[0189] The transgenic plants or plant cultivars (i.e. those obtained bygenetic engineering) which are preferably treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the. plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), and particular emphasis isgiven to maize, soya beans, potatoes, cotton and oilseed rape. Traitsthat are emphasized are in particular increased defence of the plantsagainst insects by toxins formed in the plants, in particular thoseformed in the plants by the genetic material from Bacillus thuringiensis(for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits that are alsoparticularly emphasized are the increased defence of the plants tofungi, bacteria and viruses by systemic acquired resistance (SAR),systemin, phytoalexins, elicitors and resistance genes andcorrespondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

[0190] The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention,where in addition to the good control of weed plants, the abovementionedsynergistic effects with the transgenic plants or plant cultivars occur.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

[0191] The following examples show the preparation and use of the activecompounds according to the invention:

PREPARATION EXAMPLES Example 1

[0192]

[0193] (Process (a))

[0194] A mixture of 2.80 g (8.43 mMol) of2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoicacid, 0.945 g (8.43 mMol) of 1-ethyl-5-hydroxy-pyrazole, 2.10 g (10.1mmol) of dicyclohexylcarbodiimide and 30 ml of acetonitrile is stirredat room temperature (about 20° C.) for 18 hours and then filtered. 0.335g (3.37 mMol) of trimethylsilyl cyanide and 1.70 g (16.9 mMol) oftriethylamine are added to the filtrate and the mixture is stirred atroom temperature for 18 hours and then concentrated under reducedpressure. The residue is stirred with 10% strength aqueous sodiumcarbonate solution and then shaken with diethyl ether. The organic phaseis separated off (and discarded) and the aqueous solution is thenacidified with conc. hydrochloric acid, and the resulting crystallineproduct is isolated by filtration with suction.

[0195] This gives 1.60 g (32.5% of theory) ofN-[2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenyl]-3-methyl-2-oxo-1-imidazolidinecarboxamide.

[0196] logP (pH=2.3): 1.58.

[0197] Analogously to Example 1, and in accordance with the generaldescription of the preparation process according to the invention, it isalso possible to prepare, for example, the compounds of the generalformula (I)—or of the formulae (I-1), (I-2) or (I-3) - listed in Table Ibelow. TABLE 1 (I-1)

(I-2)

(I-3)

Examples of the compounds of the formulae (I) (I-1), (I-2), (I-3) Here,Y in each case represents hydrogen Ex.- (position) (position) FormulaNo. Q R¹ R² R³ R⁴ R⁵ Z Physical Data 2 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1,39^(a) 3 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a) 4 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.32^(a) 5 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.83^(a) 6 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a) 7 O C₂H₅ H (4) CF₃ — H

(I-1) logP = 2.93^(a) 8 O CH₃ H (4) CF₃ — H

(I-1) logP = 2.50^(a) 9 O CH₃₃ H (2) Cl (4) Cl H

(I-2) logP = 1.55^(a) 10 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 0.82^(a) 11 O C₂H₅ H (4) CF₃ — H

(I-1) logP = 2.42^(a) 12 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.63^(a) 13 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.86^(a) 14 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.25^(a) 15 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.03^(a) 16 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.17^(a) 17 O CH₃ H (4) CF₃ — H

(I-1) logP = 2.12^(a) 18 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.11^(a) 19 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.83^(a) 20 O CH₃ H (2) Cl (4) Cl H

(I-2) 21 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 0.99^(a) 22 O CH₃ H (2) Cl (4) Cl H

(I-2) 23 O CH₃ H (2) Cl (4) Cl H

(I-2) 24 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.18^(a) 25 O CH₃ H (2) Cl (4) Cl H

(I-2) 26 O CH₃ H (2) Cl (4) Cl H

(I-2) 27 O CH₃ H (2) Cl (4) Cl H

(I-2) 28 O CH₃ H (2) Cl (4) Cl H

(I-2) 29 O CH₃ H (2) Cl (4) Cl H

(I-2) 30 O CH₃ H (2) Cl (4) Cl H

(I-2) 31 O CH₃ H (2) Cl (4) Cl H

(I-2) 32 O CH₃ H (2) Cl (4) Cl H

(I-2) 33 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 2.11^(a) 34 O CH₃ H (2) Cl (4) Cl H

(I-2) 35 O CH₃ H (2) Cl (4) Cl H

(I-2) 36 O CH₃ H (2) Cl (4) Cl H

(I-2) 37 O CH₃ H (2) Cl (4) Cl H

(I-2) 38 O CH₃ H (2) Cl (4) Cl H

(I-2) 39 O CH₃ H (2) Cl (4) Cl H

(I-2) 40 O CH₃ H (2) Cl (4) Cl H

(I-2) 41 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.10^(a) 42 O CH₃ H (2) Cl (4) Cl H

(I-2) 43 O CH₃ H (2) Cl (4) Cl H

(I-2) 44 O CH₃ H (2) Cl (4) Cl H

(I-2) 45 O CH₃ H (2) Cl (4) Cl H

(I-2) 46 O CH₃ H (2) Cl (4) Cl H

(I-2) 47 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.99^(a) 48 O CH₃ H (2) Cl (4) Cl H

(I-2) 49 O CH₃ H (2) Cl (4) Cl H

(I-2) 50 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 51 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 52 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 53 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 54 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 55 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 56 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 57 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 58 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 59 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 60 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 61 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 62 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 63 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 64 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 65 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 66 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 67 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 68 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 69 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 70 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 71 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 72 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 73 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 74 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 75 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 76 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 77 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 78 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 79 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 80 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 81 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 82 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 83 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 84 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 85 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 86 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 87 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 88 O CH₃ H (4) CF₃ — H

(I-1) 89 O CH₃ H (4) CF₃ — H

(I-1) 90 O C₂H₅ H (4) CF₃ — H

(I-1) 91 O CH₃ H (4) CF₃ — H

(I-1) 92 O CH₃ H (4) CF₃ — H

(I-1) 93 O CH₃ H (4) CF₃ — H

(I-1) 94 O CH₃ H (4) CF₃ — H

(I-1) 95 O C₂H₅ H (4) CF₃ — H

(I-1) 96 O C₂H₅ H (4) CF₃ — H

(I-1) 97 O CH₃ H (4) CF₃ — H

(I-1) 98 O C₂H₅ H (4) CF₃ — H

(I-1) 99 O C₂H₅ H (2) Cl (4) Cl CH₃

(I-2) logP = 1.40^(a) 100 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.42^(a) 101 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.42^(a) 102 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 3.30^(a) 103 O C₂H₅ H (4) CF₃ — CH₃

(I-1) logP = 1.78^(a) 104 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.25^(a) 105 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.33^(a) 106 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.75^(a) 107 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.50^(a) 108 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.06^(a) 109 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 0.72^(a) 110 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.52^(a) 111 O C₂H₅ H (2) OCH₃ — H

(I-3) logP = 1.74^(a) 112 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.82^(a) 113 O CH₃ H (2) Cl (4) Cl H

(I-2) 114 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 115 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 116 O CH₃

(2) Cl (4) Cl H

(I-2) 117 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 118 O

H (2) Cl (4) Cl H

(I-2) 119 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 120 O CH₃

(2) Cl (4) Cl H

(I-2) 121 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 122 O

H (2) Cl (4) Cl H

(I-2) 123 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 124 O CH₃

(2) Cl (4) Cl H

(I-4) 125 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 126 O

H (2) Cl (4) Cl H

(I-2) 127 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.07^(a) 128 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.33^(a) 129 O CH₃ H (2) Cl (4) Cl H

(I-2) 130 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 131 O CH₃ H (2) Cl (4) Cl H

(I-2) 132 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 133 O CH₃ H (2) Cl (4) Cl H

(I-2) 134 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 135 O CH₃

(2) Cl (4) Cl H

(I-2) 136 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 137 O

H (2) Cl (4) Cl H

(I-2) 138 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 139 O CH₃

(2) Cl (4) Cl H

(I-2) 140 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 141 O

H (2) Cl (4) Cl H

(I-2) 142 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 143 O CH₃ H (2) Cl (4) Cl H

(I-2) 144 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 145 O CH₃

(2) Cl (4) Cl H

(I-2) 146 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 147 O

H (2) Cl (4) Cl H

(I-2) 148 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.45^(a) 149 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.18^(a) 150 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 151 O CH₃

(2) Cl (4) Cl H

(I-2) 152 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 153 O

H (2) Cl (4) Cl H

(I-2) 154 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 155 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 156 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.54^(a) 157 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 158 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 159 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.37^(a) 160 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 161 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.11^(a) 162 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.38^(a) 163 S CH₃ H (2) Cl (4) Cl H

(I-2) 164 S C₂H₅ H (2) Cl (4) Cl H

(I-2) 165 O C₂H₅ H (4) CF₃ — H

(I-1) 166 O CH₃ H (2) NO₂ — H

(I-3) 167 O CH₃ H (4) CF₃ — H

(I-1) 168 O C₂H₅ H (2) NO₂ — H

(I-3) 169 O CH₃ H (2) OCH₃ — H

(I-1) 170 O C₂H₅ H (2) OCH₃ — H

(I-1) 171 O C₂H₅ H (2) Cl (4) Cl CH₃

(I-2) logP = 2.88^(a) 172 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.96^(a) 173 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.70^(a) 174 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.20^(a) 175 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.24^(a) 176 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.39^(a) 177 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a) 178 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.43^(a) 179 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.72^(a) 180 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a) 181 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.63^(a) 182 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.36^(a) 183 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.53^(a) 184 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.34^(a) 185 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.10^(a) 186 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.31^(a) 187 O CH₃ H (2) Cl (4) Cl H

(I-2) 188 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 189 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 190 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 191 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 192 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 193 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 194 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 195 O CH₃ H (2) Cl (4) Cl H

(I-2) 196 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 197 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 198 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 199 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 200 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 201 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 202 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 203 O CH₃ H (2) Cl (4) Cl H

(I-2) 204 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 205 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 206 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 207 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 208 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 209 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 210 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 211 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 212 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 213 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 214 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 215 O CH₃ H (2) Cl (4) Cl H

(I-2) 216 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 217 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 218 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 219 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 220 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 221 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 222 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 223 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 224 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 225 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 226 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 227 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 228 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 229 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 230 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 231 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 232 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 233 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 234 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 235 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 236 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 237 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 238 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 239 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 240 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 241 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 242 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 243 O CH₃ H (2) Cl (4) Cl H

(I-2) 244 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 245 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 246 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 247 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 248 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 249 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 250 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 251 O CH₃ H (2) Cl (4) Cl H

(I-2) 252 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 253 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 254 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 255 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 256 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 257 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 258 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 259 O CH₃ H (2) Cl (4) Cl H

(I-2) 260 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 261 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 262 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 263 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 264 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 265 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 266 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 267 O CH₃ H (2) Cl (4) Cl H

(I-2) 268 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 269 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 270 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 271 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 272 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 273 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 274 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 275 O CH₃ H (2) Cl (4) Cl H

(I-2) 276 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 277 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 278 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 279 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 280 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 281 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 282 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 283 O CH₃ H (2) Cl (4) Cl H

(I-2) 284 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 285 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 286 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 287 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 288 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 289 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 290 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 291 S CH₃ H (2) Cl (4) Cl H

(I-2) 292 S C₂H₅ H (2) Cl (4) Cl H

(I-2) 293 S CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 294 S C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 295 S CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 296 S C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 297 5 CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 298 S C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 299 S CH₃ H (2) Cl (4) Cl H

(I-2) 300 S C₂H₅ H (2) Cl (4) Cl H

(I-2) 301 S CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 302 S C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 303 S CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 304 S C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 305 S CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 306 S C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2)

[0198] (a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—the corresponding measurement resultsin Table 1 are marked ^(a)).

[0199] (b) Mobile phases for the determination in the neutral range:0.01 molar aqueous phosphate buffer solution, acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile—the correspondingmeasurement results in Table 1 are marked ^(b)).

[0200] Calibration was carried out using unbranched alkan-2-ones (having3 to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanols).

[0201] The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (III) Example (III-1)

[0202]

[0203] A mixture of 11.3 g (32.9 mMol) of methyl2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoate,50 ml of water, 50 ml of tetrahydrofuran and 1.3 g of sodium hydroxideis stirred at room temperature (about 20° C.) for 18 hours and thenconcentrated under reduced pressure to about half its original volume.The mixture is then shaken with diethyl ether, the organic phase isseparated off (and discarded) and the aqueous phase is acidified withconc. hydrochloric acid. The resulting crystalline product is isolatedby filtration with suction.

[0204] This gives 9.1 g (81.5% of theory) of2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoicacid.

[0205] logP (pH=2.3): 1.35.

[0206] Analogously to Example (III-1), it is also possible to prepare,for example, the compounds of the general formula (III) listed in Table2 below.

TABLE 2 Examples of the compounds of the formula (III) (position)(position) (position) Physical Data Ex.-No. R³ R⁴

III-2 (2) (4) (3) logP = 1.17^(a)) Cl Cl

III-3 (2) (4) (3) Cl Cl

III-4 (2) (4) (3) logP = 1.58^(a)) Cl Cl

III-5 (2) (4) (3) Cl Cl

III-6 (2) (4)

logP = 0.78 a) Cl Cl (3) III-7 (2) (4) (3) logP = 1.05^(a)) Cl Cl

III-8 (2) (4)

Cl Cl (3) III-9 (4) — (2) logP = 2.43^(a)) CF₃

III-10 (4) — (2) logP = 2.13^(a)) CF₃

III-11 (4) — (2) CF₃

III-12 (4) — (2) CF₃

III-13 (4) —

CF₃ (2) III-14 (4) — (2) CF₃

III-15 (4) —

CF₃ (2)

Starting Materials of the Formula (IIIa) Example (IIIa-1)

[0207]

[0208] A mixture of 12.3 g (50 mMol) of methyl2,4-dichloro-3-isocyanato-benzoate, 5.0 g (50 mmol) of1-methyl-2-oxo-imidazolidine, a few drops of triethylamine and 100 ml ofacetonitrile is stirred at room temperature (about 20° C.) for 18 hoursand then concentrated under reduced pressure. The residue is thendigested with diethyl ether and the crystalline product is isolated byfiltration with suction.

[0209] This gives 11.4 g (60% of theory) of methyl2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoate.

[0210] logP (pH=2.3): 1.94.

[0211] Analogously to Example (IIIa-1) it is also possible to prepare,for example, the compounds of the general formula (IIIa) listed in Table3 below.

TABLE 3 Examples of the compounds of the formula (IIIa) (position)(position) (position) Physical Data Ex.-No. R R₃ R₄

IIIa-2 CH₃ (2) (4) (3) Cl Cl

IIla-3 CH₃ (2) (4) (3) Cl Cl

IIIa-4 CH₃ (2) (4) (3) Cl Cl

IIIa-5 CH₃ (2) (4) (3) Cl Cl

IIIa-6 CH₃ (2) (4)

logP = 1.34^(a)) Cl Cl (3) IIIa-7 CH₃ (2) (4) (3) logP = 1.64^(a)) Cl Cl

IIIa-8 CH₃ (2) (4)

logP = 0.50^(a)) Cl Cl (3) IIIa-9 CH₃ (4) — (2) logP = 3.35^(a)) CF₃

IIIa-10 CH₃ (4) — (2) logP = 2.76^(a)) CF₃

IIIa-11 CH₃ (4) — (2) CF3

IIIa-12 CH₃ (4) — (2) CF₃

IIIa-13 CH₃ (4) —

CF₃ (2) IIIa-14 CH₃ (4) — (2) CF₃

IIIa-15 CH₃ (4) —

CF₃ (2) IIIa-16 CH₃ (2) (4) (3) Cl Cl

Use Examples Example A Pre-emergence Test

[0212] Solvent: 5 parts by weight of acetone Emulsifier: 1 part byweight of alkylarylpolyglycol ether

[0213] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0214] Seeds of the test plants are sown in normal soil. After 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of active compound in the spray liquor is chosensuch that the particular amount of active compound desired is applied in1000 litres of water per hectare.

[0215] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control. Thefigures denote:

[0216] 0%=no effect (like untreated control)

[0217] 100%=total destruction

[0218] In this test, for example, the compounds of Preparation Examples1, 2, 3, 4, 5 and 6 exhibit strong activity against weeds, and some aretolerated well by crop plants, such as, for example, maize.

Example B Post-emergence Test

[0219] Solvent: 5 parts by weight of acetone Emulsifier: 1 by weight ofalkylarylpolyglycol ether

[0220] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0221] Test plants of a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen such that the particular amounts of activecompound desired are applied in 1000 1 of water/ha.

[0222] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control.

[0223] The figures denote:

[0224] 0%=no effect (like untreated control)

[0225] 100%=total destruction

[0226] In this test, for example, the compounds of Preparation Examples1, 2, and 5 exhibit strong activity against weeds.

1. Compounds of the general formula (I),

in which Q represents O (oxygen) or S (sulphur), R¹ represents in eachcase optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R²represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkoxy, alkylthio,alkoxycarbonyl or cycloalkyl, R³, R⁴ independently of one anotherrepresent hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or in each case optionally substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino,dialkylaminocarbonyl or dialkylaminosulphonyl, R⁵ represents hydrogen orrepresents in each case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aryl, arylthio, arylsulphinyl, arylsulphonyl,arylalkyl, or represents the grouping —C(Q)—Z, Y represents hydrogen orin each case optionally substituted alkyl, alkylsulphonyl,alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,alkenyl, alkenylsulphonyl, alkenylcarbonyl, alkinyl, alkinylcarbonyl,cycloalkyl, cycloalkylcarbonyl, cycloalkylalkyl, phenyl,phenylsulphonyl, phenylcarbonyl, phenylalkyl, phenylalkylsulphonyl,phenylalkylcarbonyl or phenylcarbonylalkyl, and Z represents amino,cyanoamino, nitroamino, hydroxyamino, hydrazino, represents in each casecyano-, alkoxy-, alkylthio-, alkylsulphinyl- oralkylsulphonyl-substituted alkyl, alkoxy, alkylthio or alkylamino,represents in each case optionally substituted alkylcarbonyl,alkoxycarbonyl, alkoxyamino, alkylhydrazino, alkylcarbonylhydrazino,alkoxycarbonylhydrazino, alkylsulphonylhydrazino, N-alkyl-alkoxyamino,dialkylhydrazino, alkenyloxy, alkenylamino, alkenyloxyamino, alkinyloxy,alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino,cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy,arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino, the grouping —N=(heterocyclyl),heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio orheterocyclylalkylamino, including all possible tautomeric forms of thecompounds of the general formula (I) and the possible salts of thecompounds of the general formula (I).
 2. Compounds of the formula (I)according to claim 1, characterized in that Q represents O (oxygen), R¹represents optionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl having 1to 6 carbon atoms, represents in each case optionally cyano- orhalogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, or represents optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, R²represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy or alkoxycarbonyl having in eachcase up to 6 carbon atoms, represents optionally halogen-substitutedalkylthio having 1 to 6 carbon atoms, or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms, R³, R⁴ independently of one another represent hydrogen, nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represent in eachcase optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy,alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4carbon atoms in the alkyl groups, or represent alkylamino, dialkylamino,dialkylaminocarbonyl or dialkylaminosulphonyl having in each case up to4 carbon atoms in the alkyl groups, R⁵ represents hydrogen, representsin each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substitutedalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl having in eachcase 1 to 6 carbon atoms in the alkyl groups, represents in each caseoptionally cyano- or halogen-substituted alkenyl or alkinyl having ineach case 3 to 6 carbon atoms in the alkenyl and alkinyl groups,respectively, represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in eachcase 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1to 4 carbon atoms in the alkyl moiety, represents in each caseoptionally nitro- cyano-, C₁-C₄-alkyl-, C₁-C₄-halogenalkyl-,C₁-C₄-alkoxy-, C₁-C₄-halogenalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenalkylthio-, C₁-C₄-alkylsulphinyl-,C₁-C₄-halogenalkylsulphinyl-, C₁-C₄-alkylsulphonyl- orC₁-C₄-halogenalkylsulphonyl-substituted aryl, arylthio, arylsulphinyl,arylsulphonyl or arylalkyl having in each case 6 or 10 carbon atoms inthe aryl groups and, if appropriate, 1 to 4 carbon atoms in the alkylmoiety, or represents the grouping —C(Q)—Z, Y represents hydrogen,represents optionally cyano-, carbamoyl-, halogen-, C₁-C₄-alkoxy- orC₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,represents optionally halogen-substituted alkylsulphonyl having 1 to 6carbon atoms, represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl oralkylaminocarbonyl having in each case 1 to 6 carbon atoms in the alkylgroups, represents dialkylaminocarbonyl having 1 to 4 carbon atoms inthe alkyl groups, represents in each case optionally cyano- orhalogen-substituted alkenyl, alkenylcarbonyl, alkinyl or alkinylcarbonylhaving in each case up to 6 carbon atoms, represents optionallyhalogen-substituted alkenylsulphonyl having up to 6 carbon atoms,represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkylcarbonyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl groups and, if appropriate, 1 to 3 carbon atoms in the alkylmoiety, or represents in each case optionally nitro-, cyano-,carbamoyl-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-or C₁-C₄-halogenalkoxy-substituted phenyl, phenylsulphonyl,phenylcarbonyl, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl-sulphonyl,phenyl-C₁-C₄-alkylcarbonyl or phenylcarbonyl-C₁-C₄-alkyl, and Zrepresents amino, cyanoamino, nitroamino, hydroxyamino, hydrazino,represents in each case cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy,alkylthio or alkylamino having in each case 1 to 6 carbon atoms,represents C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxycarbonyl, represents ineach case optionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkoxyamino,alkylhydrazino, alkylcarbonylhydrazino, alkoxycarbonylhydrazino oralkylsulphonylhydrazino having in each case 1 to 6 carbon atoms in thealkyl groups, represents N-alkyl-alkoxyamino or dialkylhydrazino havingin each case 1 to 4 carbon atoms in the alkyl groups, represents in eachcase optionally halogen-substituted alkenyloxy, alkenylamino,alkenyloxyamino, alkinyloxy or alkinylamino having in each case 2 to 6carbon atoms, represents in each case optionally cyano-, halogen- orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylamino,cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy orcycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkylmoiety, represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenalkoxy- or C₁-C₄-alkoxy-carbonyl-substituted aryl,arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino,arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylaminohaving in each case 6 or 10 carbon atoms in the aryl group and, ifappropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents ineach case optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-,C₃-C₆-cycloalkyl-, C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted monocyclic or bicyclic heterocyclyl,heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy, heterocyclylalkylthio, heterocyclylalkylamino or thegrouping —N═(heterocyclyl), where in each case the heterocyclyl groupingcontains up to 10 carbon atoms and additionally at least one heteroatomselected from the group consisting of nitrogen (but at most 5 N atoms),oxygen (but at most 2 O atoms), sulphur (but at most 2 S atoms), SO orSO₂ and, if appropriate, additionally one group selected from the groupconsisting of oxo (C═O), thioxo (C═S), imino (C═NH), cyanoimino(C═N—CN), nitroimino (C═N—NO₂) and where, if appropriate, the alkylmoiety contains 1 to 4 carbon atoms.
 3. Compounds of the formula (I)according to claim 1, characterized in that R¹ represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, represents in each case optionallycyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl,propinyl or butinyl, or represents in each case optionally cyano-,fluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R² representshydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, represents in each case optionally fluorine- and/orchlorine-substituted methylthio, ethylthio, n- or i-propylthio, orrepresents in each case optionally cyano-, fluorine-, chlorine-,bromine- methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, R³, R⁴ independently of one another representhydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, iodine, represent in each case optionally fluorine-,chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, represent methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,dimethylamino, diethylamino, dimethylaminocarbonyl,diethylaminocarbonyl, dimethylaminosulphonyl or diethylaminosulphonyl,R⁵ represents hydrogen, represents in each case optionally cyano-,fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-,i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-,s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, representsdimethylamino or diethylamino, represents in each case optionallyfluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl,butenyl, pentenyl, ethinyl, propinyl, butinyl or pentinyl, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-,s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio,phenylsulphinyl, phenylsulphonyl, naphthyl, phenylmethyl, phenylethyl,naphthylmethyl or naphthylethyl or represents the grouping —C(Q)—Z, Yrepresents hydrogen, represents in each case optionally cyano-,carbamoyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedmethyl, ethyl, n- or i-propyl, represents in each case optionallyfluorine- and/or chlorine-substituted methylsulphonyl, ethylsulphonyl,n- or i-propylsulphonyl, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substitutedacetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- ori-propylaminocarbonyl, represents dimethylaminocarbonyl ordiethylaminocarbonyl, represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyl, butenyl,propenylcarbonyl, butenylcarbonyl, propinyl, butinyl, propinylcarbonylor butinylcarbonyl, represents in each case optionally fluorine- and/orchlorine-substituted propenylsulphonyl or butenylsulphonyl, representsin each case optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, carbamoyl-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyl, phenylsulphonyl, phenylcarbonyl,phenylmethyl, phenylethyl, phenylmethylsulphonyl, phenylmethylcarbonylor phenylcarbonylmethyl, and Z represents amino, cyanoamino, nitroamino,hydroxyamino, hydrazino, represents in each case cyano-, methoxy-,ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino,n- or i-propylamino, n-, i-, s- or t-butylamino, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methoxyamino,ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino,methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- ort-butylhydrazino, N-methyl-methoxyamino or dimethylhydrazino, representsin each case optionally fluorine-, chlorine- and/or bromine-substitutedpropenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio,pentenylthio, propenylamino, butenylamino, pentenylamino,propenyloxyamino, butenyloxyamino, pentenyloxyamino, propinyloxy,butinyloxy, pentinyloxy, propinylamino, butinylamino or pentinylamino,represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino,cyclohexylamino, cyclopropylhydrazino, cyclobutylhydrazino,cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-,methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl,naphthyloxy, naphthylthio, naphthylamino, phenylmethyl, phenylethyl,phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio,phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl,naphthylmethoxy, naphthylethoxy, naphthylmethylamino ornaphthylethylamino, or represents in each case optionally nitro-,cyano-, fluorine-, chlorinebromine-, methyl-, ethyl-, n- or i-propyl-,n-, i-, s- or t-butyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-,cyclohexyl-, difluoromethyl-, trifluormethyl-, dichloromethyl-,trichloromethyl, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-,ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-,s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedmonocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,the grouping —N═(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy orheterocyclylalkylamino from the group consisting of furyl, furyloxy,furylamino, furylmethyl, furylmethoxy, furylmethylamino,tetrahydrofuryl, tetrahydrofuryloxy, tetrahydrofurylamino,tetrathydrofurylmethyl, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanylmethyl,dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolinyl, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinyl,2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl (oxazolinyl),tetrahydrooxazolyl (oxazolidinyl), isoxazolyl, dihydroisoxazolyl(isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),tetrahydro-(2H)-1,2-oxazin-2-yl, oxazolylmethyl, thiazolyl,dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl),thiazolimino, thiazolylmethyl, dihydrothiazolyl (thiazolinyl),tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl,cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino,oxotriazolinyl, oxotetrazolinyl, dioxanyl, dioxanylmethyl,dioxanylmethoxy, dioxanylmethylamino, dithianyl, dithianylmethyl,dithianylmethoxy, dithianylmethylamino, triazolylamino, piperidinyl,piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl,2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl,oxomorpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy,pyridinylamino, 2-(1H)-pyridinimino, pyridinylmethyl, pyridinylmethoxy,pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy. 4.Compounds of the formula I) according to claim 1, characterized in thatR¹ represents methyl, ethyl, n- or i-propyl, cyclopropyl, cyclopentyl orcyclohexyl, R² represents hydrogen, represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,methoxycarbonyl or ethoxycarbonyl, represents in each case optionallyfluorine- and/or chlorine-substituted methylthio or ethylthio, orrepresents optionally fluorine-, chlorine- or methyl-substitutedcyclopropyl, R³, R⁴ independently of one another represent hydrogen,nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, difluoromethyl, trifluoromethyl, dichloromethyl,trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, R⁵ represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n- or i-butyl, represents methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- ori-propylamino or dimethylamino, represents in each case optionallyfluorine- and/or chlorine-substituted propenyl, butenyl, propinyl orbutinyl, represents in each case optionally cyano-, fluorine-, chlorine-or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-,s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio,phenylsulphinyl, phenylsulphonyl, phenylmethyl or phenylethyl, orrepresents the grouping —C(Q)—Z, Y represents hydrogen, represents ineach case optionally cyano-, fluorine-, methoxy-, ethoxy-,methoxycarbonyl- or ethoxycarbonyl-substituted methyl or ethyl,represents in each case optionally fluorine- and/or chlorine-substitutedmethylsulphonyl or ethylsulphonyl, represents in each case optionallycyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted acetyl,propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl orethylaminocarbonyl, represents dimethylaminocarbonyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted propenyl,propenylcarbonyl, propinyl or propinylcarbonyl, represents in each caseoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylsulphonyl, phenylcarbonyl,phenylmethyl, phenylmethylsulphonyl, phenylmethylcarbonyl orphenylcarbonylmethyl, and Z represents amino, cyanoamino, hydrazino,represents in each case optionally cyano-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n-or i-propylamino, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substitutedmethoxyamino, ethoxyamino, n- or i-propoxyamino, methylhydrazino,ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino,represents N-methylmethoxyamino or dimethylhydrazino, represents in eachcase optionally fluorine- and/or chlorine-substituted propenyloxy,butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino,propenyloxyamino, butenyloxyamino, propinyloxy, butinyloxy,propinylamino or butinylamino, represents in each case optionallycyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopentylhydrazino,cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino orcyclohexylmethylamino, represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluormethyl-, methoxy-, ethoxy-,n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl,phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino,phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy,phenylmethylthio, phenylethylthio, phenylmethylamino orphenylethylamino, or or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl,n-, i-, s- or t-butyl-, cyclohexyl-, difluoromethyl-, trifluoromethyl-,dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-,fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- ori-propylthio-, difluoromethylthio-, trifluoromethylthio-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedmonocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,the grouping —N═(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy orheterocyclylalkylamino from the group consisting of furyl, furyloxy,furylamino, furylmethyl, furylmethoxy, furylmethylamino,tetrahydrofuryl, tetrahydrofuryloxy, tetrahydrofurylamino,tetrahydrofurylmethyl, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanylmethyl,dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolinyl, imidazolylmethyl, imidazolinylmethyl,2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl(oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl,dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),tetra-hydro-(2H)-1,2-oxazin-2-yl, thiazolyl, thiazolylmethyl,dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl),thiazolimino, oxothiazolidinyl, cyanoiminothiazolidinyl,oxadiazolylamino, thiadiazolylamino, oxotriazolinyl, oxotetrazolinyl,dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino,dithianyl, dithianylmethyl, dithianylmethoxy, dithianylmethylamino,triazolylamino, piperidinyl, piperidinylamino, oxopiperidinyl,2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxo-morpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,2-(1H)-pyridinimino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl,pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy.
 5. Compounds ofthe formula (I) according to claim 1, characterized in that Q representsO (oxygen) or S (sulphur), R¹ represents methyl, ethyl, n- or i-propyl,R² represents hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl,methylthio or ethylthio, R³, R⁴ independently of one another representhydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl,difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl,methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, R⁵ represents hydrogen, represents methyl,ethyl, n- or i-propyl, represents methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl or ethylsulphonyl, represents in each case optionallyfluorine- and/or chlorine-substituted propenyl, butenyl, propinyl orbutinyl, or represents cyclopropyl, Y represents hydrogen, represents ineach case optionally cyano-, fluorine-, methoxy-, ethoxy-,methoxycarbonyl- or ethoxycarbonyl-substituted methyl or ethyl,represents in each case optionally fluorine- and/or chlorine-substitutedmethylsulphonyl or ethylsulphonyl, represents in each case optionallycyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted acetyl,propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl orethylaminocarbonyl, represents dimethylaminocarbonyl, represents in eachcase optionally fluorine-, chlorine- or bromine-substituted propenyl,propenylcarbonyl, propinyl or propinylcarbonyl, represents in each caseoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylsulphonyl, phenylcarbonyl,phenylmethyl, phenylmethylsulphonyl, phenylmethylcarbonyl orphenylcarbonylmethyl and Z represents amino, cyanoamino, hydrazino,represents methoxyamino, ethoxyamino, n- or i-propoxyamino,methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- ort-butylhydrazino, represents N-methyl-methoxyamino or dimethylhydrazino,represents in each case optionally fluorine- and/or chlorine-substitutedpropenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino,butenylamino, propenyloxyamino, butenyloxyamino, propinyloxy,butinyloxy, propinylamino or butinylamino, represents in each caseoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy,cyclohexyloxy, cyclopropylamino, cyclopentylamino, cyclohexylamino,cyclohexylhydrazino, cyclopropylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclopentylmethoxy,cyclohexylmethoxy, cyclopropylmethylamino, cyclopentylmethylamino orcyclohexylmethylamino, represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl,phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino,phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy,phenylmethylthio, phenylethylthio, phenylmethylamino orphenylethylamino, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-,cyclohexyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-,trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-,difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic orbicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino from thegroup consisting of furyl, furyloxy, furylamino, furylmethyl,furylmethoxy, furylmethylamino, tetrahydrofuryl, tetrahydrofuryloxy,tetrahydrofurylamino, tetrahydrofurylmethyl, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,thienylmethyl, thienylmethylamino, dithiolanyl, dithiolanylmethyl,dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolinyl, imidazolylmethyl, imidazolinylmethyl,2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl(oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl,dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),thiazolyl, thiazolylmethyl, dihydrothiazolyl (thiazolinyl),tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl,cyanoiminothiazolidinyl, oxotriazolinyl, oxotetrazolinyl, dioxanyl,dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, dithianyl,dithianylmethyl, dithianylmethoxy, dithianylmethylamino, triazolylamino,piperidinyl, piperidinylamino, oxopiperidinyl,2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxomorpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy,pyrimidinylmethyl, pyrimidinylmethoxy.
 6. Process for preparingcompounds of the formula (I) according to claim 1, characterized in that(a) pyrazoles of the general formula (II)

 in which  R¹, R² and Y are as defined in claim 1  are reacted withsubstituted benzoic acids of the general formula (III)

 in which  Q, R³, R⁴, R⁵ and Z are as defined in claim 1  — or withreactive derivatives thereof—  if appropriate in the presence of adehydrating agent, if appropriate in the presence of one or morereaction auxiliaries and if appropriate in the presence of one or morediluents,  or that (b) substituted benzoylpyrazoles of the generalformula (Ia)

 in which  Q, R¹, R², R³, R⁴, R⁵ and Z are as defined in claim 1,  arereacted with compounds of the general formula (IV) X—Y  (IV)  in which Y is as defined in claim 1, except for hydrogen, and  X representshalogen,  — or, if appropriate, with corresponding acid anhydrides,isocyanates or isothiocyanates—  if appropriate in the presence of oneor more reaction auxiliaries and if appropriate in the presence of oneor more diluents,  and, if appropriate, the resulting compounds of theformula (I) are subsequently subjected, in a customary manner, toelectrophilic or nucleophilic substitution reactions and/or oxidation orreduction reactions, or the compounds of the formula (I) are, in acustomary manner, converted into salts.
 7. Compounds of the formula(I-a)

in which Q, R¹, R², R³, R⁴, R⁵ and Z are as defined in claim
 1. 8.Herbicidal compositions, characterized in that they comprise at leastone compound according to any of claims 1 to 5 and customary extenders.9. Use of at least one compound according to any of claims 1 to 5 or acomposition according to claim 8 for controlling undesirable plants. 10.Method for controlling undesirable plants, characterized in that atleast one compound according to any of claims 1 to 5 or a compositionaccording to claim 8 is allowed to act on the undesirable plants, and/ortheir habitat.